Monomer, polymer, compensation film, optical film, and display device

ABSTRACT

wherein in Chemical Formula 1-1, Z, L1, L2, R1 to R6, n, m, p, and a to f are the same as defined in the detailed description.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a divisional of U.S. patent application Ser. No.15/242,862 filed in the United States Patent and Trademark Office onAug. 22, 2016, which claims priority to Korean Patent Application No.10-2015-0121502 filed in the Korean Intellectual Property Office on Aug.28, 2015, and all the benefits accruing therefrom under 35 U.S.C. § 119,the contents of both applications being incorporated herein in theirentireties by reference.

BACKGROUND 1. Field

A monomer, a polymer, a compensation film, an optical film, and adisplay device are disclosed.

2. Description of the Related Art

A flat panel displays may be classified into a light-emitting displaydevice emitting light by itself and a non-emissive display devicerequiring a separate light source, and a compensation film or an opticalfilm is frequently employed for improving the image quality thereof.There still remains a need in novel polymers, which can improve theproperties of the existing compensation and optical films.

SUMMARY

An embodiment provides a novel monomer that is applicable to acompensation film.

Another embodiment provides a polymer including a moiety derived fromthe novel monomer by polymerization of the novel monomer.

Yet another embodiment provides a compensation film including thepolymer.

Still another embodiment provides an optical film including thecompensation film.

A further embodiment provides a display device including thecompensation film or the optical film.

According to an embodiment, a monomer represented by Chemical Formula1-1 is provided.

In Chemical Formula 1-1,

Z is —O—, —C═O—, —(C═O)O—, —O(C═O)—, —CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—,—CH═CH—, —CF═CF—, or —C(═O)NR^(a)—,

L¹ and L² are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC1 to C20 oxyalkylene group, a substituted or unsubstituted C3 to C20cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C20 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C20 divalent heterocyclic group, or acombination thereof,

R¹ to R⁶ and R^(a) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof,

n and m are independently 0 or 1,

p is an integer ranging from 1 to 3,

a to f are independently integers ranging from 0 to 4, and

a+b, c+d, and e+f are independently integers of less than or equal to 4.

The monomer may be represented by Chemical Formula 1-1a or 1-1b.

In Chemical Formulae 1-1a and 1-1b,

Z is —C═O—, —(C═O)O—, —O(C═O)—, —CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—,—CH═CH—, —CF═CF—, or —C(═O)NR^(a)—,

L¹ and L² are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC1 to C20 oxyalkylene group, a substituted or unsubstituted C3 to C20cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C20 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C20 divalent heterocyclic group, or acombination thereof,

R¹ to R⁶ and R^(a) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof, p isan integer ranging from 1 to 3,

a to f are independently integers ranging from 0 to 4, and

a+b, c+d, and e+f are independently integers of less than or equal to 4.

The monomer may be represented by Chemical Formula 1a or 1b.

According to another embodiment, a polymer, which is a reaction productof an anhydride and a diamine compound, wherein the diamine compoundincludes a first diamine compound represented by Chemical Formula 1-1,is provided.

The first diamine compound may be represented by Chemical Formula 1-1aor 1-1b.

The first diamine compound may be represented by Chemical Formula 1a or1b.

The diamine compound may further include a second diamine compound,which is different from the first diamine compound, wherein the seconddiamine compound may include at least one selected from compounds ofGroup 1.

In Group 1,

R³² to R⁴⁸ are independently hydrogen, a substituted or unsubstituted C1to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxygroup, a substituted or unsubstituted C1 to C20 fluoroalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyl group, a substitutedor unsubstituted C3 to C20 heterocyclic group, a substituted orunsubstituted C3 to C20 cycloalkoxy group, a substituted orunsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6 toC20 aryloxy group, a substituted or unsubstituted amine group, asubstituted or unsubstituted C1 to C20 alkylamine group, a substitutedor unsubstituted silyl group, a hydroxy group, a halogen, a nitro group,or a combination thereof,

X² to X¹⁰ are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20arylene group, a substituted or unsubstituted C3 to C20 divalentheterocyclic group, —SO₂—, —O—, —C(═O)—, —C(═O)O—, a group selected fromGroup 2, or a combination thereof,

n35 to n37 and n40 to n49 are independently an integer ranging from 0 to4, and

n38 and n39 are independently an integer ranging from 0 to 3.

The second diamine compound may include at least one selected fromcompounds of Group 3.

A mole ratio of the first diamine compound and the second diaminecompound may be about 1:9 to about 5:5.

The anhydride may be represented by Chemical Formula 2 or 3.

In Chemical Formula 2 or 3,

L³ is a single bond, a substituted or unsubstituted C1 to C20 alkylenegroup, a substituted or unsubstituted C1 to C20 oxyalkylene group, asubstituted or unsubstituted C3 to C20 cycloalkylene group, asubstituted or unsubstituted C3 to C20 oxycycloalkylene group, asubstituted or unsubstituted C6 to C20 arylene group, a substituted orunsubstituted C6 to C20 oxyarylene group, a substituted or unsubstitutedC3 to C20 divalent heterocyclic group, —O—, —C(═O)—, —C(═O)O—, —SO₂—, or—C(═O)NR^(b)—, or a combination thereof, and

R⁷ to R¹² and R^(b) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof.

The anhydride may include 2,3,3′,4′-biphenyltetracarboxylic dianhydride,2,3,3′,4′-diphenylsulfone tetracarboxylic dianhydride,3,4′-oxydiphthalic anhydride, 3,3′,4,4′-biphenyl tetracarboxylicdianhydride, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylicdianhydride, 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride,4,4′-(hexafluoroisopropylidene)diphthalic anhydride, 4,4′-oxydiphthalicanhydride, pyromellitic dianhydride,4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylicanhydride, or a combination thereof.

According to another embodiment, a compensation film includes a polymer,which is a reaction product of an anhydride and a diamine compound,wherein the polymer includes a side chain including at least oneacetylene group.

The diamine compound may include a first diamine compound represented byChemical Formula 1-2.

In Chemical Formula 1-2,

Z is —O═O—, —(C═O)O—, —O(C═O)—, —CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—,—CH═CH—, —CF═CF—, or —C(═O)NR^(a)—,

L¹ and L² are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC1 to C20 oxyalkylene group, a substituted or unsubstituted C3 to C20cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C20 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C20 divalent heterocyclic group, or acombination thereof,

R¹ to R⁶ and R^(a) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof,

n and m are independently 0 or 1,

p is an integer ranging from 0 to 3, for example p is an integer rangingfrom 1 to 3,

a to f are independently integers ranging from 0 to 4, and

a+b, c+d, and e+f are independently integers of less than or equal to 4.

The first diamine compound may be represented by Chemical Formula 1-2aor 1-2b.

In Chemical Formulae 1-2a and 1-2b,

Z is —C═O—, —(C═O)O—, —O(C═O)—, —CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—,—CH═CH—, —CF═CF—, or —C(═O)NR^(a)—,

L¹ and L² are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC1 to C20 oxyalkylene group, a substituted or unsubstituted C3 to C20cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C20 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C20 divalent heterocyclic group, or acombination thereof,

R¹ to R⁶ and R^(a) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof, and

p is an integer ranging from 0 to 3, for example p is an integer rangingfrom 1 to 3,

a to f are independently integers ranging from 0 to 4, and

a+b, c+d, and e+f are independently integers of less than or equal to 4.

The first diamine compound may be represented by one of ChemicalFormulae 1a to 1d.

The diamine compound may include a second diamine compound, which isdifferent from the first diamine compound, wherein the second diaminecompound may include at least one selected from compounds of Group 1.

The second diamine compound may include at least one selected from Group3.

A mole ratio of the first diamine compound and the second diaminecompound may be about 1:9 to about 5:5.

The anhydride may be represented by Chemical Formula 2 or 3.

The anhydride may include 2,3,3′,4′-biphenyltetracarboxylic dianhydride,2,3,3′,4′-diphenylsulfone tetracarboxylic dianhydride,3,4′-oxydiphthalic anhydride, 3,3′,4,4′-biphenyl tetracarboxylicdianhydride, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylicdianhydride, 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride,4,4′-(hexafluoroisopropylidene)diphthalic anhydride, 4,4′-oxydiphthalicanhydride, pyromellitic dianhydride,4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylicanhydride, or a combination thereof.

The compensation film may be elongated in a uniaxial direction.

Retardation of the compensation film at a 550 nanometer wavelength maybe about 110 nanometers to about 160 nanometers.

Retardation values (R) of the compensation film at a 450 nanometerwavelength, a 550 nanometer wavelength, and a 650 nanometer wavelengthmay satisfy one of Relationship Equations 1 to 5.

R(450 nanometers)≤R(550 nanometers)<R(650 nanometers)  RelationshipEquation 1

R(450 nanometers)<R(550 nanometers)≤R(650 nanometers)  RelationshipEquation 2

R(450 nanometers)≥R(550 nanometers)>R(650 nanometers)  RelationshipEquation 3

R(450 nanometers)>R(550 nanometers)≥R(650 nanometers)  RelationshipEquation 4

R(450 nanometers)=R(550 nanometers)=R(650 nanometers)  RelationshipEquation 5

According to another embodiment, an optical film includes thecompensation film and a polarization film.

The polarization film may be made of a melt-blend of a hydrophobicpolymer and a dichroic dye.

According to yet another embodiment, a display device includes thecompensation film or the optical film.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects, advantages and features of this disclosurewill become more apparent by describing in further detail exemplaryembodiments thereof with reference to the accompanying drawings, inwhich:

FIG. 1 is a schematic cross-sectional view showing an optical filmaccording to an embodiment;

FIG. 2 is a schematic view showing the anti-reflection principle of anoptical film according to an embodiment;

FIG. 3 is a schematic view showing an example of a polarization film;

FIG. 4 is a schematic cross-sectional view showing an organic lightemitting diode (OLED) device according to an embodiment; and

FIG. 5 is a schematic cross-sectional view showing a liquid crystaldisplay (LCD) device according to an embodiment.

DETAILED DESCRIPTION

Exemplary embodiments of the present disclosure will hereinafter bedescribed in detail, and may be easily performed by those who havecommon knowledge in the related art. However, this disclosure may beembodied in many different forms, and is not construed as limited to theexemplary embodiments set forth herein.

In the drawings, the thickness of layers, films, panels, regions, etc.,are exaggerated for clarity. Like reference numerals designate likeelements throughout the specification. It will be understood that whenan element such as a layer, film, region, or substrate is referred to asbeing “on” another element, it can be directly on the other element orintervening elements may also be present. In contrast, when an elementis referred to as being “directly on” another element, there are nointervening elements present.

Accordingly, the embodiments are merely described below, by referring tothe figures, to explain aspects of the present description. As usedherein, the term “and/or” includes any and all combinations of one ormore of the associated listed items. The term “or” means “and/or.”Expressions such as “at least one of” when preceding a list of elements,modify the entire list of elements and do not modify the individualelements of the list.

It will be understood that when an element is referred to as being “on”another element, it may be directly on the other element or interveningelements may be present therebetween. In contrast, when an element isreferred to as being “directly on” another element, there are nointervening elements present.

It will be understood that, although the terms first, second, third etc.may be used herein to describe various elements, components, regions,layers and/or sections, these elements, components, regions, layersand/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer orsection from another element, component, region, layer, or section.Thus, a first element, component, region, layer, or section discussedbelow could be termed a second element, component, region, layer, orsection without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise. The term“or” means “and/or.” As used herein, the term “and/or” includes any andall combinations of one or more of the associated listed items.Expressions such as “at least one of,” when preceding a list ofelements, modify the entire list of elements and do not modify theindividual elements of the list.

It will be further understood that the terms “comprises” and/or“comprising,” or “includes” and/or “including” when used in thisspecification, specify the presence of stated features, regions,integers, steps, operations, elements, and/or components, but do notpreclude the presence or addition of one or more other features,regions, integers, steps, operations, elements, components, and/orgroups thereof.

“About” or “approximately” as used herein is inclusive of the statedvalue and means within an acceptable range of deviation for theparticular value as determined by one of ordinary skill in the art,considering the measurement in question and the error associated withmeasurement of the particular quantity (i.e., the limitations of themeasurement system).

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this general inventive conceptbelongs. It will be further understood that terms, such as those definedin commonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand the present disclosure, and will not be interpreted in an idealizedor overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to crosssection illustrations that are schematic illustrations of idealizedembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, embodiments described herein should not beconstrued as limited to the particular shapes of regions as illustratedherein but are to include deviations in shapes that result, for example,from manufacturing. For example, a region illustrated or described asflat may, typically, have rough and/or nonlinear features. Moreover,sharp angles that are illustrated may be rounded. Thus, the regionsillustrated in the figures are schematic in nature and their shapes arenot intended to illustrate the precise shape of a region and are notintended to limit the scope of the present claims.

“Mixture” as used herein is inclusive of all types of combinations,including blends, alloys, solutions, and the like.

As used herein, when specific definition is not otherwise provided, theterm “substituted” refers to one substituted with a substituent selectedfrom a halogen (F, Br, Cl, or I), a hydroxy group, an alkoxy group, anitro group, a cyano group, an amino group, an azido group, an amidinogroup, a hydrazino group, a hydrazono group, a carbonyl group, acarbamoyl group, a thiol group, an ester group, a carboxyl group or asalt thereof, a sulfonic acid group or a salt thereof, phosphoric acidor a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, aC2 to C20 alkynyl group, a C6 to C30 aryl group, a C7 to C30 arylalkylgroup, a C1 to C30 alkoxy group, a C1 to C20 heteroalkyl group, a C3 toC20 heteroarylalkyl group, a C3 to C30 cycloalkyl group, a C3 to C15cycloalkenyl group, a C6 to C15 cycloalkynyl group, a C3 to C30heterocycloalkyl group, and a combination thereof, instead of hydrogenof a compound or a group.

When a group containing a specified number of carbon atoms issubstituted with any of the groups listed in the preceding paragraph,the number of carbon atoms in the resulting “substituted” group isdefined as the sum of the carbon atoms contained in the original(unsubstituted) group and the carbon atoms (if any) contained in thesubstituent. For example, when the term “substituted C1 to C20 alkyl”refers to a 01 to C20 alkyl group substituted with a C6 to C20 arylgroup, the total number of carbon atoms in the resulting arylsubstituted alkyl group is C7 to C40.

As used herein, when a definition is not otherwise provided, the term“alkyl” indicates a group derived from a completely saturated, branchedor unbranched (or a straight or linear) hydrocarbon and having aspecified number of carbon atoms.

As used herein, when a definition is not otherwise provided, the term“alkoxy” represents “alkyl-O—”, wherein the term “alkyl” has the samemeaning as described above.

As used herein, when a definition is not otherwise provided, the term“alkoxyalkyl” indicates an alkyl group substituted with one or morealkoxy groups, wherein the terms “alkyl” and “alkoxy” have the samemeaning as described above.

As used herein, when a definition is not otherwise provided, the term“fluoroalkyl” indicates an alkyl group substituted with one or morefluorine groups, wherein the term “alkyl” has the same meaning asdescribed above.

As used herein, when a definition is not otherwise provided, the term“cycloalkyl” indicates a monovalent group having one or more saturatedrings in which all ring members are carbon.

As used herein, when a definition is not otherwise provided, the term“cycloalkyloxy” represents “cycloalkyl-O—”, wherein the term“cycloalkyl” has the same meaning as described above.

As used herein, when a definition is not otherwise provided, the term“cycloalkoxyalkyl” indicates an alkyl group substituted with one or morecycloalkoxy groups, wherein the terms “alkyl” and “cycloalkoxy” have thesame meaning as described above.

As used herein, when a definition is not otherwise provided, the term“aryl” indicates a group derived from an aromatic hydrocarbon containingat least one ring and having the specified number of carbon atoms.

As used herein, when a definition is not otherwise provided, the term“silyl” indicates “R₃Si—”, wherein each R is independently “hydrogen”,“alkyl” or “aryl” having the same meaning as described above.

As used herein, the term “alkylene” indicates a straight or branchedsaturated aliphatic hydrocarbon group having a valence of at least two,optionally substituted with one or more substituents where indicated,provided that the valence of the alkylene group is not exceeded.

As used herein, when a definition is not otherwise provided, the term“oxyalkylene” indicates an alkylene group in which any one or moremethylene groups (—CH₂—) is substituted with an oxygen group (—O—),wherein the term “alkylene” has the same meaning as described above.

As used herein, the term “cycloalkylene” indicates a divalent grouphaving one or more saturated rings in which all ring members are carbon,optionally substituted with one or more substituents where indicated,provided that the valence of the cycloalkylene group is not exceeded.

As used herein, when a definition is not otherwise provided, the term“oxycycloalkylene” indicates a cycloalkylene group in which any one ormore methylene groups (—CH₂—) is substituted with an oxygen group (—O—),wherein the term “cycloalkylene” has the same meaning as describedabove.

As used herein, when a definition is not otherwise provided, the term“arylene” indicates a divalent group formed by the removal of twohydrogen atoms from one or more rings of an arene, wherein the hydrogenatoms may be removed from the same or different rings of the arene.

As used herein, when a definition is not otherwise provided, the term“oxyarylene” represents “-arylene-O—” or “—O-arylene-”, wherein the term“arylene” has the same meaning as described above.

As used herein, when a definition is not otherwise provided, the term“alkylarylene” indicates an arylene group substituted with an alkylenegroup, wherein the terms “arylene” and “alkylene” have the same meaningas described above.

As used herein, when a definition is not otherwise provided, the term“arylalkylene” indicates an alkylene group substituted with an arylenegroup, wherein the terms “alkylene” and “arylene” have the same meaningas described above.

As used herein, when specific definition is not otherwise provided, theterm “‘hetero” refers to one including 1 to 3 heteroatoms selected fromN, O, S, Se, and P.

As used herein, when specific definition is not otherwise provided, theterm “‘heterocyclic group” refers to C1 to C20 heteroaryl group, forexample C2 to C8 heteroaryl group, including 1 to 3 heteroatoms selectedfrom N, O, S, Se, and P, or C1 to C20 heterocycloalkyl group, forexample C3 to C8 to heterocycloalkyl group, including 1 to 3 heteroatomsselected from N, O, S, Se, and P.

Hereinafter, a monomer according to an embodiment is described.

A monomer according to an embodiment is represented by Chemical Formula1-1.

In Chemical Formula 1-1,

Z is —O═O—, —(C═O)O—, —O(C═O)—, —CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—,—CH═CH—, —CF═CF—, or —C(═O)NR^(a)—,

L¹ and L² are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC1 to C20 oxyalkylene group, a substituted or unsubstituted C3 to C20cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C20 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C20 divalent heterocyclic group, or acombination thereof,

R¹ to R⁶ and R^(a) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof,

n and m are independently 0 or 1, p is an integer ranging from 1 to 3,

a to f are independently integers ranging from 0 to 4, and

a+b, c+d, and e+f are independently integers of less than or equal to 4.

For example, L¹ and L² may be independently a single bond, a substitutedor unsubstituted C1 to C6 alkylene group, a substituted or unsubstitutedC1 to C20 oxyalkylene group, a substituted or unsubstituted C3 to C8cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C12 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C8 divalent heterocyclic group, or acombination thereof.

The monomer is a diamine compound including an acetylene group, and maybe used as a reagent of a polyimide and/or polyamic acid.

The monomer may be, for example, represented by Chemical Formula 1-1a or1-1b.

In Chemical Formulae 1-1a and 1-1b, Z, L², R¹ to R⁶, n, m, p and a to fare the same as defined in Chemical Formula 1-1.

The monomer may be, for example, represented by Chemical Formula 1a or1b.

Hereinafter, a polymer according to an embodiment is described.

A polymer according to an embodiment is a reaction product of ananhydride and a diamine compound, and the polymer may include a moietyderived from a first diamine compound represented by Chemical Formula1-1.

In Chemical Formula 1-1,

Z is —C═O—, —(C═O)O—, —O(C═O)—, —CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—,—CH═CH—, —CF═CF—, or —C(═O)NR^(a)—,

L¹ and L² are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC1 to C20 oxyalkylene group, a substituted or unsubstituted C3 to C20cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C20 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C20 divalent heterocyclic group, or acombination thereof,

R¹ to R⁶ and R^(a) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof,

n and m are independently 0 or 1,

p is an integer ranging from 1 to 3,

a to f are independently integers ranging from 0 to 4, and

a+b, c+d, and e+f are independently integers of less than or equal to 4.

The polymer may be a polyimide, polyamic acid, or a combination thereof.

The polymer may include a main chain containing a polyimide, polyamicacid, or a combination thereof obtained by a reaction of an anhydrideand a diamine compound, and a side chain including an acetylene groupderived from the first diamine compound represented by Chemical Formula1-1. The side chain including an acetylene group may be arranged in asubstantially vertical direction with respect to the main chain, and mayprovide the polymer with predetermined modified optical properties.

The first diamine compound may be, for example, represented by ChemicalFormula 1-1a or 1-1 b.

In Chemical Formulae 1-1a and 1-1b, Z, L², R¹ to R⁶, n, m, p and a to fare the same as defined in Chemical Formula 1-1.

The first diamine compound may be, for example, represented by ChemicalFormula 1a or 1b.

The diamine compound may further include a second diamine compound,which is different from the first diamine compound, in addition to thefirst diamine compound. One or more of the second diamine compound maybe used.

The second diamine compound may, for example, include at least oneselected from compounds of Group 1.

In Group 1,

R³² to R⁴⁸ are independently hydrogen, a substituted or unsubstituted C1to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxygroup, a substituted or unsubstituted C1 to C20 fluoroalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyl group, a substitutedor unsubstituted C3 to C20 heterocyclic group, a substituted orunsubstituted C3 to C20 cycloalkoxy group, a substituted orunsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6 toC20 aryloxy group, a substituted or unsubstituted amine group, asubstituted or unsubstituted C1 to C20 alkylamine group, a substitutedor unsubstituted silyl group, a hydroxy group, a halogen, a nitro group,or a combination thereof,

X² to X¹⁰ are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20arylene group, a substituted or unsubstituted C3 to C20 divalentheterocyclic group, —SO₂—, —O—, —O(═O)—, —O(═O)O—, a group selected fromGroup 2, or a combination thereof,

n35 to n37 and n40 to n49 are independently an integer ranging from 0 to4, and

n38 and n39 are independently an integer ranging from 0 to 3.

The second diamine compound may include at least one selected fromcompounds of Group 3, but is not limited thereto.

The first diamine compound and the second diamine compound may beincluded in a mole ratio of about 1:9 to about 9:1, for example about1:9 to about 5:5.

The anhydride may be, for example, represented by Chemical Formula 2 or3.

In Chemical Formula 2 or 3,

L³ is a single bond, a substituted or unsubstituted C1 to C20 alkylenegroup, a substituted or unsubstituted C1 to C20 oxyalkylene group, asubstituted or unsubstituted C3 to C20 cycloalkylene group, asubstituted or unsubstituted C3 to C20 oxycycloalkylene group, asubstituted or unsubstituted C6 to C20 arylene group, a substituted orunsubstituted C6 to C20 oxyarylene group, a substituted or unsubstitutedC3 to C20 divalent heterocyclic group, —O—, —C(═O)—, —C(═O)O—, —SO₂—,—C(═O)NR^(b)—, or a combination thereof, and

R⁷ to R¹² and R^(b) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof.

The anhydride may include, for example,2,3,3′,4′-biphenyltetracarboxylic dianhydride, 2,3,3′,4′-diphenylsulfonetetracarboxylic dianhydride, 3,4′-oxydiphthalic anhydride,3,3′,4,4′-biphenyl tetracarboxylic dianhydride (BPDA),bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (BTDA),3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride (DSDA),4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA),4,4′-oxydiphthalic anhydride (ODPA), pyromellitic dianhydride (PMDA),4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylicanhydride (DTDA), or a combination thereof, but is not limited thereto.

The anhydride and the diamine compound may be, for example, included ina mole ratio of about 1:9 to about 9:1, for example about 3:7 to about7:3, and in another example about 5:5.

The polymer may be, for example, prepared in a form of a thin film, andmay be used as a polymer film. The polymer film may be, for example,transparent, and may be used for articles requiring transparency. Thepolymer film may be, for example, used as a substrate, a protectivefilm, an optical film, a dielectric layer, an insulation layer, anadhesive layer, and the like.

Hereinafter, a compensation film according to an embodiment is provided.

A compensation film according to an embodiment includes a polymer, whichis a reaction product of an anhydride and a diamine compound, whereinthe polymer includes a side chain including at least one acetylenegroup.

The polymer may be a polyimide, polyamic acid, or a combination thereof.

The polymer may include a main chain containing a polyimide, polyamicacid, or a combination thereof obtained by a reaction of an anhydrideand a diamine compound, and a side chain including at least oneacetylene group. The side chain of the polymer may be arranged in asubstantially vertical direction with respect to the main chain of thepolymer, and may modify light absorption characteristics depending on arefractive index and a wavelength, and thus a phase delay due to thepresence of at least one acetylene group in the side chain. For example,the polymer may adjust a refractive index (n_(e)) in a main chaindirection and a refractive index (n_(o)) in a side chain direction, andthus control birefringence depending on a wavelength.

The side chain of the polymer may be derived from the diamine compound,and the diamine compound may further include at least one substituted orunsubstituted arylene group in addition to the above at least oneacetylene group.

One or more of the diamine compound may be used, and the diaminecompound may include, for example, a first diamine compound representedby Chemical Formula 1-2.

In Chemical Formula 1-2,

Z is —C═O—, —(C═O)O—, —O(C═O)—, —CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—,—CH═CH—, —CF═CF—, or —C(═O)NR^(a)—,

L¹ and L² are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC1 to C20 oxyalkylene group, a substituted or unsubstituted C3 to C20cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C20 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C20 divalent heterocyclic group, or acombination thereof,

R¹ to R⁶ and R^(a) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof,

n and m are independently 0 or 1,

p is an integer ranging from 0 to 3,

a to f are independently integers ranging from 0 to 4, and

a+b, c+d, and e+f are independently integers of less than or equal to 4.

The first diamine derivative may be, for example, represented byChemical Formula 1-2a or 1-2b.

In Chemical Formulae 1-2a and 1-2b, Z, L², R¹ to R⁶, n, m, p and a to fare the same as defined in Chemical Formula 1-2.

The first diamine compound may be, for example, represented by one ofChemical Formulae 1a to 1d, but is not limited thereto.

The diamine compound may further include a second diamine compound,which is different from the first diamine compound, in addition to thefirst diamine compound. One or more of the second diamine compound maybe used.

The second diamine compound may, for example, include at least oneselected from compounds of Group 1.

In Group 1, R³² to R⁴⁸ are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C1 to C20fluoroalkyl group, a substituted or unsubstituted C3 to C20 cycloalkylgroup, a substituted or unsubstituted C3 to C20 heterocyclic group, asubstituted or unsubstituted C3 to C20 cycloalkoxy group, a substitutedor unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6to C20 aryloxy group, a substituted or unsubstituted amine group, asubstituted or unsubstituted C1 to C20 alkylamine group, a substitutedor unsubstituted silyl group, a hydroxy group, a halogen, a nitro group,or a combination thereof,

X² to X¹⁰ are independently a single bond, a substituted orunsubstituted C1 to C20 alkylene group, a substituted or unsubstitutedC3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20arylene group, a substituted or unsubstituted C3 to C20 divalentheterocyclic group, —SO₂—, —O—, —C(═O)—, —O(═O)O—, a group selected fromGroup 2, or a combination thereof,

n35 to n37 and n40 to n49 are independently an integer ranging from 0 to4, and

n38 and n39 are independently an integer ranging from 0 to 3.

The second diamine compound may include at least one selected fromcompounds of Group 3, but is not limited thereto.

The first diamine compound and the second diamine compound may beincluded in a mole ratio of about 1:9 to about 9:1, for example about1:9 to about 5:5.

The anhydride may be, for example, represented by Chemical Formula 2 or3.

In Chemical Formula 2 or 3,

L³ is a single bond, a substituted or unsubstituted C1 to C20 alkylenegroup, a substituted or unsubstituted C1 to C20 oxyalkylene group, asubstituted or unsubstituted C3 to C20 cycloalkylene group, asubstituted or unsubstituted C3 to C20 oxycycloalkylene group, asubstituted or unsubstituted C6 to C20 arylene group, a substituted orunsubstituted C6 to C20 oxyarylene group, a substituted or unsubstitutedC3 to C20 divalent heterocyclic group, —O—, —C(═O)—, —C(═O)O—, —SO₂—,—C(═O)NR^(b)—, or a combination thereof, and

R⁷ to R¹² and R^(b) are independently hydrogen, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C2 to C20alkoxyalkyl group, a substituted or unsubstituted C1 to C20 fluoroalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to

C20 aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof.

The anhydride may include, for example,2,3,3′,4′-biphenyltetracarboxylic dianhydride, 2,3,3′,4′-diphenylsulfonetetracarboxylic dianhydride, 3,4′-oxydiphthalic anhydride,3,3′,4,4′-biphenyl tetracarboxylic dianhydride (BPDA),bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (BTDA),3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride (DSDA),4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA),4,4′-oxydiphthalic anhydride (ODPA), pyromellitic dianhydride (PMDA),4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylicanhydride (DTDA), or a combination thereof, but is not limited thereto.

The anhydride and the diamine compound may be, for example, included ina mole ratio of about 1:9 to about 9:1, for example about 3:7 to about7:3, and in another example about 5:5.

The compensation film may be, for example, elongated in a uniaxialdirection.

As described above, the compensation film may have modified lightabsorption characteristics depending on a refractive index and awavelength due to the polymer having at least one acetylene group in theside chain, and thus may have desirable phase delay characteristics byvarying the number of the acetylene groups and length of the side chain.

For example, the compensation film may have retardation ranging fromabout 110 nanometers (nm) to about 160 nm at a wavelength of about 550nm (hereinafter called a “reference wavelength”). Herein, theretardation may be in-plane retardation or thickness directionretardation. The retardation of the compensation film at a wavelength ofabout 550 nm may be, for example, in a range of about 120 nm to about150 nm within the above broader range.

The retardation of the compensation film may be the same or differentdepending on a wavelength.

For example, the compensation film may have a reverse wavelengthdispersion phase delay in which retardation regarding light at a longwavelength is greater than retardation regarding light at a shortwavelength, and herein, the retardation (R) of the compensation filmregarding light at a wavelength of about 450 nm, about 550 nm, and about650 nm may satisfy Relationship Equation 1 or 2.

R(450 nm)≤R(550 nm)<R(650 nm)  Relationship Equation 1

R(450 nm)<R(550 nm)≤R(650 nm)  Relationship Equation 2

For example, the compensation film may have a normal wavelengthdispersion phase delay in which retardation regarding light at a longwavelength is less than retardation regarding light at a shortwavelength, and herein, the retardation (R) of the compensation filmregarding light at a wavelength of about 450 nm, about 550 nm, and about650 nm may satisfy Relationship Equation 3 or 4.

R(450 nm)≥R(550 nm)>R(650 nm)  Relationship Equation 3

R(450 nm)>R(550 nm)≥R(650 nm)  Relationship Equation 4

For example, the compensation film may have a flat wavelength dispersionphase delay in which retardation regarding light at a long wavelength issubstantially equal to retardation regarding light at a shortwavelength, and herein, the retardation (R) of the compensation filmregarding light at a wavelength of about 450 nm, about 550 nm, and about650 nm may satisfy Relationship Equation 5.

R(450 nm)=R(550 nm)=R(650 nm)  Relationship Equation 5

The compensation film may have high birefringence and thus a relativelylow thickness. The compensation film may have, for example, a thicknessof about 3 micrometers (μm) to about 100 μm, for example, a thickness ofabout 5 μm to about 70 μm, and in another example, a thickness of about5 μm to about 30 μm.

The compensation film includes a substantially transparent polymer,which may be used as a substrate, and accordingly, a separate substratemay be omitted beneath the compensation film. Accordingly, thecompensation film may be much thinner. The compensation film may beeffectively applied to a flexible display device such as a foldabledisplay device or a bendable display device, and thus improve opticalproperties and display characteristics.

The compensation film may be, for example, manufactured by a methodincluding providing a composition, transforming the composition into athin film, and curing the thin film.

The composition may include an anhydride, a diamine compound, and asolvent. The anhydride and diamine compound are the same as describedabove. The solvent may be, for example, an aprotic polar solvent, forexample a sulfoxide-containing solvent such as dimethylsulfoxide anddiethylsulfoxide, a formamide-containing solvent such asN,N-dimethylformamide and N,N-diethylformamide, an acetamide-containingsolvent such as N,N-dimethylacetamide, N,N-di methylmethoxyacetamide,and N,N-diethylacetamide, a pyrrolidone-containing solvent such asN-methyl-2-pyrrolidone (NMP), N-acetyl-2-pyrrolidone, andN-vinyl-2-pyrrolidone, a halogenated phenol such as o-cresol, m-cresol,p-cresol, and xylenol, and a phenol-containing solvent such as catechol,hexamethylphosphoramide, γ-butyrolactone, tetrahydrothiophene dioxide,N-methyl-δ-caprolactam, N,N,N′,N′-tetramethylurea, or a mixture thereof,but is not limited thereto.

The anhydride and the diamine compound may be, for example, included ina mole ratio of about 1:9 to about 9:1, for example about 3:7 to about7:3, and in another example about 5:5.

The anhydride and the diamine compound may be included in an amount ofabout 10 to about 80 percent by weight (wt %), for example about 30 toabout 60 wt %, based on the total amount of the composition. The solventmay be included in a balance amount except the anhydride and the diaminecompound in the composition.

The composition may be, for example, coated by spin coating, slitcoating, inkjet coating, dip coating, and the like, but is not limitedthereto.

The curing may be, for example, performed at about 50 to about 120° C.,for example about 70 to about 100° C.

The compensation film may be, for example, elongated in a uniaxialdirection. The compensation film may be, for example, elongated at anelongation rate of about 200% to about 1,000% at a temperature of about50° C. to about 500° C. Herein the elongation rate refers to a lengthratio of after the elongation to before the elongation of thecompensation film, and means the elongation extent of the compensationfilm after uniaxial elongation.

The compensation film may be used alone or with another compensationfilm.

The compensation film may be used with a polarization film to provide anoptical film for preventing reflection of external light of a displaydevice. The optical film may be, for example, an antireflective film,but is not limited thereto.

FIG. 1 is a schematic cross-sectional view showing an optical filmaccording to an embodiment, FIG. 2 is a schematic view showing theanti-reflection principle of an optical film according to an embodiment,and FIG. 3 is a schematic view showing an example of a polarizationfilm.

Referring to FIG. 1, an optical film 100 according to an embodimentincludes a polarization film 110 and a compensation film 120. Thecompensation film 120 may circularly polarize light passing through thepolarization film 110 and thus cause retardation and have an influenceon reflection and/or absorption of the light.

For example, the optical film 100 may be disposed on one side or bothsides of a display device, and particularly, on the screen side of thedisplay device, and thus may prevent reflection of light flowing in fromthe outside (hereinafter referred to as “reflection of external light”).Therefore, the optical film 100 may prevent visibility deterioration dueto the reflection of external light.

FIG. 2 is a schematic view showing the external light anti-reflectionprinciple of an optical film according to an embodiment.

Referring to FIG. 2, while the incident unpolarized light having enteredfrom the outside is passed through the polarization film 110, and thepolarized light is shifted into circularly polarized light by passingthrough the compensation film 120, only a first polarized perpendicularcomponent, which is one polarized perpendicular component of twopolarized perpendicular components, is transmitted. While the circularlypolarized light is reflected in a display panel 50 including asubstrate, an electrode, and so on, is changed in the circularpolarization direction, and is passed through the compensation film 120again, only a second polarized perpendicular component, which is theother polarized perpendicular component of the two polarizedperpendicular components, may be transmitted. As the second polarizedperpendicular component is not passed through the polarization film 110,and light does not exit to the outside, an effect of preventing theexternal light reflection may be provided.

Referring to FIG. 3, the polarization film 110 has a self-integratedstructure which is made of a melt blend of a polymer 71 and a dichroicdye 72.

The polymer 71 may be, for example, a hydrophobic polymer, for example apolyolefin such as polyethylene (PE), polypropylene (PP), and acopolymer thereof; a polyamide such as nylon and an aromatic polyamide,a polyester such as polyethylene terephthalate (PET), glycol modifiedpolyethylene terephthalate (PETG), and polyethylene naphthalate (PEN); apolyacrylate such as polymethyl(meth)acrylate; a polystyrene such aspolystyrene (PS) and an acrylonitrile-styrene copolymer; apolycarbonate; a vinyl chloride type polymer; a polyimide; a polysulfoneresin; a polyethersulfone; a polyether-etherketone; a polyphenylenesulfide; a vinyl alcohol type polymer; a vinylidene chloride typepolymer; a vinyl butyral type polymer; an allylic polymer; apolyoxymethylene; an epoxy polymer; a copolymer thereof; or acombination thereof.

Among them, the polymer 71 may be, for example, a polyolefin, apolyamide, a polyester, a polyacrylate, a polystyrene, a copolymerthereof, or a combination thereof, and in another example, polyethylene(PE), polypropylene (PP), polyethylene terephthalate (PET), glycolmodified polyethylene terephthalate (PETG), polyethylene naphthalate(PEN), nylon, a copolymer thereof, or a combination thereof.

The polymer 71 may be a polyolefin. The polyolefin may be, for example,a mixture of at least two selected from polyethylene (PE), polypropylene(PP), and a copolymer of polyethylene and polypropylene (PE-PP), and inanother example, a mixture of polypropylene (PP) and apolyethylene-polypropylene copolymer (PE-PP).

The polymer 71 may have transmittance of greater than or equal to about85% in a wavelength region of about 400 nm to about 780 nm. The polymer71 is elongated in a uniaxial direction. The uniaxial direction may bethe same as a length direction of the dichroic dye 72.

The dichroic dye 72 is dispersed into the polymer 71, and is aligned inthe elongation direction of the polymer 71. The dichroic dye 72 maytransmit one perpendicular polarization component of two perpendicularpolarization components in a predetermined wavelength region.

The dichroic dye 72 may be included in an amount of about 0.01 to about5 parts by weight, based on 100 parts by weight of the polymer 71. Whilenot wishing to be bound by theory, it is understood that within theabove range, sufficient polarization characteristics may be obtainedwithout deteriorating transmittance of a polarization film. Within theabove broader range, the dichroic dye 72 may be included in an amount ofabout 0.05 to about 1 part by weight, based on 100 parts by weight ofthe polymer 71.

The polarization film 110 may have a relatively low thickness of lessthan or equal to about 100 μm, for example about 30 μm to about 95 μm.While not wishing to be bound by theory, it is understood that when thepolarization film 110 has a thickness within the range, it may besignificantly thinner than a polarizing plate requiring a protectivelayer such as triacetyl cellulose (TAC), and may contribute to realizinga thin display device.

The compensation film 120 is the same as described above.

The optical film 100 may further include a correction layer (not shown)positioned on one side of the compensation film 120. The correctionlayer may be, for example, a color shift resistant layer, but is notlimited thereto.

The optical film 100 may further include a light blocking layer (notshown) extended along the edge. The light blocking layer may be formedin a strip along the circumference of the optical film 100, and forexample, may be positioned between the polarization film 110 and thecompensation film 120.

The light blocking layer may include an opaque material, for example, ablack material. For example, the light blocking layer may be made of ablack ink.

The optical film 100 may be applied to various display devices.

A display device according to an embodiment includes a display panel andan optical film positioned on the display panel. The display panel maybe a liquid crystal display panel or an organic light emitting displaypanel, but is not limited thereto.

Hereinafter, an organic light emitting diode device is described as anexample of a display device.

FIG. 4 is a schematic cross-sectional view showing an organic lightemitting diode (OLED) device according to an embodiment.

Referring to FIG. 4, the organic light emitting diode device accordingto an embodiment includes an organic light emitting display panel 400and an optical film 100 positioned on the organic light emitting displaypanel 400. The organic light emitting display panel 400 may include abase substrate 410, a lower electrode 420, an organic emission layer430, an upper electrode 440, and an encapsulation substrate 450.

The base substrate 410 may be made of glass or plastic.

At least one of the lower electrode 420 and the upper electrode 440 maybe an anode, and the other may be a cathode. The anode is an electrodeinjected with holes, and it may be made of a transparent conductivematerial having a high work function to transmit the emitted light tothe outside, for example, ITO or IZO. The cathode is an electrodeinjected with electrons, and it may be made of a conductive materialhaving a low work function without affecting the organic material, andmay be selected from, for example, aluminum (Al), calcium (Ca), andbarium (Ba).

The organic emission layer 430 includes an organic material which mayemit light when a voltage to the lower electrode 420 and the upperelectrode 440 is applied.

An auxiliary layer (not shown) may be further provided between the lowerelectrode 420 and the organic emission layer 430, and between the upperelectrode 440 and the organic emission layer 430. The auxiliary layer isused to balance electrons and holes, and may include a hole transportlayer, a hole injection layer (HIL), an electron injection layer (EIL),and an electron transporting layer.

The encapsulation substrate 450 may be made of glass, metal, or apolymer, and may seal the lower electrode 420, the organic emissionlayer 430, and the upper electrode 440 to prevent moisture and/or oxygeninflow from the outside.

The optical film 100 may be disposed on the light-emitting side. Forexample, in the case of a bottom emission structure emitting light atthe side of the base substrate 410, the optical film 100 may be disposedon the exterior side of the base substrate 410, while in the case of atop emission structure emitting light at the side of the encapsulationsubstrate 450, the optical film 100 may be disposed on the exterior sideof the encapsulation substrate 450.

The optical film 100 includes the integrated polarization film 110 andthe integrated compensation film 120. The polarization film 110 and thecompensation film 120 are respectively the same as described above, andmay prevent a display device from having visibility deterioration causedby light inflowing from the outside after passing the polarization film110 and being reflected by a metal such as an electrode and the like inthe organic light emitting display panel 400. Accordingly, displaycharacteristics of the organic light emitting diode device may beimproved.

Hereinafter, a liquid crystal display (LCD) device is described as anexample of the display device.

FIG. 5 is a schematic cross-sectional view showing a liquid crystaldisplay (LCD) device according to an embodiment.

Referring to FIG. 5, the liquid crystal display (LCD) according to anembodiment includes a liquid crystal display panel 500, and an opticalfilm 100 positioned on the liquid crystal panel 500.

The liquid crystal panel 500 may be a twist nematic (TN) mode panel, apatterned vertical alignment (PVA) mode panel, an in-plane switching(IPS) mode panel, an optically compensated bend (OCB) mode panel, or thelike.

The liquid crystal panel 500 may include a first display panel 510, asecond display panel 520, and a liquid crystal layer 530 interposedbetween the first display panel 510 and the second display panel 520.

The first display panel 510 may include, for example, a thin filmtransistor (not shown) formed on a substrate (not shown) and a firstelectric field generating electrode (not shown) connected to the same,and the second display panel 520 may include, for example, a colorfilter (not shown) formed on a substrate (not shown) and a secondelectric field generating electrode (not shown). However, it is notlimited thereto, and the color filter may be included in the firstdisplay panel 510, while the first electric field generating electrodeand the second electric field generating electrode may be disposed onthe first display panel 510 together therewith.

The liquid crystal layer 530 may include a plurality of liquid crystalmolecules. The liquid crystal molecules may have positive or negativedielectric anisotropy. In the case of the liquid crystal moleculeshaving positive dielectric anisotropy, the major axes thereof may bealigned substantially parallel to the surface of the first display panel510 and the second display panel 520 when an electric field is notapplied, and the major axes may be aligned substantially perpendicularto the surface of the first display panel 510 and second display panel520 when an electric field is applied. On the other hand, in the case ofthe liquid crystal molecules having negative dielectric anisotropy, themajor axes may be aligned substantially perpendicular to the surface ofthe first display panel 510 and the second display panel 520 when anelectric field is not applied, and the major axes may be alignedsubstantially parallel to the surface of the first display panel 510 andthe second display panel 520 when an electric field is applied.

The optical film 100 may be disposed on the outside of the liquidcrystal panel 500. Although the optical film 100 is shown to be providedon both the lower part and the upper part of the liquid crystal panel500 in the drawing, it is not limited thereto, and it may be formed ononly one of the lower part and the upper part of the liquid crystalpanel 500.

The optical film 100 includes the integrated polarization film 110 andthe integrated compensation film 120, which are the same as describedabove.

Hereinafter, the present disclosure is illustrated in more detail withreference to examples. However, these examples are illustrative only,and the present disclosure is not limited thereto.

Synthesis of Monomer Synthesis Example 1: Synthesis of Compound 1Synthesis of Intermediate I-1

1-bromo-4-iodobenzene (mw=282.91 grams per mole (g/mol), v=0.5 moles(mol), m=141.46 grams (gr)) is dissolved in 1.5 liters (L) of a mixedsolvent of triethylamine and tetrahydrofuran (volume to volume (v/v) of1:1) in a 2 L round-bottomed flask to prepare a solution. Subsequently,the solution is purged with dry nitrogen gas for 1 hour (h).Subsequently, phenylacetylene (mw=102.14 g/mol, v=0.5 mol, m=51.1 gr),palladium(II) chloride (PdCl₂, mw=177.33 g/mol, v=0.005 mol, m=0.89 gr),copper(I) iodide (Cul) (mw=190.45 g/mol, v=0.01 mol, m=1.9 gr), andtriphenylphosphine (PPh₃, mw=262.45 g/mol, v=0.02 mol, m=5.25 gr) aresequentially added to the solution. Then, the mixture is stirred at 25°C. for 8 h and at 60° C. for 12 h under a nitrogen atmosphere.Subsequently, 2-methyl-3-butyn-2-ol (mw=84.12 g/mol, v=0.6 mol, m=50.5gr), palladium(II) chloride (PdCl₂, mw=177.33 mol, v=0.0025 mol, m=0.45gr), copper(I) iodide (Cul) (mw=190.45 g/mol, v=0.005 mol, m=0.95 gr),and triphenylphosphine (PPh₃, mw=262.45 g/mol, v=0.01 mol, m=2.63 gr)are sequentially added thereto, and the mixture is stirred at 100° C.for 48 h under a nitrogen atmosphere. When the reaction is complete, thesuspension is filtered to obtain a precipitate, and the precipitate iswashed several times with a small amount of hot ethyl acetate. Then, thesolvent is removed from the mother liquor under a reduced pressure, andthe remaining solid is crystallized from ethyl acetate. The motherliquid is concentrated after the crystallization and dried at 60° C.under vacuum to obtain an intermediate I-1. The yield of theintermediate 1-1 is 88.3%.

Synthesis of Intermediate I-2

Intermediate I-1 (mw=260.34 mol, v=0.1 mol, m=26.3 gr) is dissolved in0.5 L of toluene in a 1 L round-bottomed flask, and 32 milliliters (ml)of Bu₄NOH (10 percent by weight (wt %) in MeOH, 0.1 equivalents (eq.);d=0.82 grams per cubic centimeter (g/cm³)) is added thereto. When thereaction is complete, the mixture is neutralized with acetic acid, andthe solvent is removed therefrom under a reduced pressure. The obtainedyellow solid is washed with water and dried at 60° C. under vacuum toobtain a yellow solid intermediate I-2. The yield of the intermediateI-2 is 95%.

Synthesis of Intermediate I-3

1,3-dinitrobenzene (mw=168.11 g/mol, v=0.6 mol, m=100.9 gr) is stirredand dissolved in 220 ml of H₂SO₄ (98 wt %) in a 1 L round-bottomed flaskat 80° C. Subsequently, N-bromosuccinimide (mw=177.98 g/mol, v=0.9 mol,m=160.18 gr) is divided into 3 portions and separately added thereto.First, 0.6 mol of the N-bromosuccinimide is added to the solution, andthe obtained mixture is stirred for 24 h, secondly, 0.18 mol of theN-bromosuccinimide is added thereto, and the obtained mixture is stirredfor 24 h, and thirdly, 0.12 mol of the N-bromosuccinimide is addedthereto, and the obtained mixture is stirred for 72 h. When the reactionis complete, the mixture is poured into 1 kilogram (kg) of ice to form ayellow solid. Subsequently, the yellow solid is filtered and washed withwater. The obtained product is consecutively crystallized four timesfrom a small amount of iso-propanol to obtain a green crystalline solidof an intermediate I-3. The yield of the intermediate I-3 is 52.1%.

Synthesis of Intermediate I-4

Intermediate I-2 (mw=202.26 g/mol, v=0.123 mol, m=24.88 gr) and theintermediate I-3 (mw=247.01 g/mol, v=0.123 mol, m=30.38 gr) aredissolved in 600 ml of triethylamine in a 1 L round-bottomed flask toprepare a solution. Subsequently, the solution is purged with drynitrogen gas for 1 h. Then, palladium(II) chloride (PdCl₂, mw=177.33g/mol, v=0.00123 mol, m=0.22 gr), copper(I) iodide (Cul) (mw=190.45g/mol, v=0.00246 mol, m=0.47 gr), and triphenylphosphine (PPh₃,mw=262.45 g/mol, v=0.00492 mol, m=1.29 gr) are sequentially added to thesolution, and the mixture is refluxed at 100° C. for 24 h under anitrogen atmosphere. When the reaction is complete, triethylamine isremoved therefrom under reduced pressure, and the remaining solid iswashed with water. The obtained product is suspended in hot iso-propanoland then filtered while cooled, which is repeated twice. The resultingproduct is dried at 80° C. under vacuum to obtain a light yellowcrystalline solid of an intermediate I-4. The yield of the intermediateI-4 is 98.2%.

Synthesis of Final Compound (Compound 1)

Intermediate I-4 (mw=368.35 g/mol, v=0.119 mol, m=44 gr) is suspended ina boiling mixed solvent of 180 ml of acetic acid and 3 L of methanol ina 5 L flask. Subsequently, iron powder (mw=55.85 g/mol, v=0.952 mol,m=53.2 gr) is added to the suspension, and 100 ml of water is addedthereto. Then, the mixture is refluxed for 6 h, and 200 ml of water isfurther added thereto. When the reaction is complete, 1 L of water isfurther added thereto, and the solid obtained by cooling down theobtained mixture is collected by filtration. Subsequently, the obtainedsolid is suspended in 300 ml of boiling methanol and then filtered whilebeing cooled, which is repeated three times. The obtained product isdissolved in 300 ml of dimethyl acetamide and filtered, and thenreprecipitated in 2 L of water. Subsequently, the precipitate isfiltered and then suspended in iso-propanol to remove water therefrom.The obtained product is collected by filtration, and the obtained solidis suspended in 600 ml of boiling methanol and then filtered while beingcooled. Then, the product obtained therefrom is dried at 70° C. undervacuum to obtain compound 1. The yield of the compound 1 is 67.1%.

¹H NMR (DMSO-d6) 300 MHz, δ, ppm: 4.92 (s, 4H, NH₂), 5.88 (dd, 1H,J¹³=1.8 Hz), 6.00 (d, 2H, J¹³=1.8 Hz), 7.45-7.58 (m, 9H).

Synthesis Example 2: Synthesis of Compound 2 Synthesis of IntermediateI-5

3.5-dinitrobenzoic acid (mw=212.12 g/mol, v=0.2 mol, m=42.42 gr),phosphorus pentachloride (PCl₅, mw=208.24 g/mol, v=0.2 mol, m=41.65 gr)and one drop of pyridine are added to 300 ml of toluene, and the mixtureis stirred and refluxed for 12 h. Subsequently, toluene and POCl₃ areremoved under reduced pressure, and the remaining residue is dissolvedin 1 L of dichloromethane. Subsequently,1-[2-(4-hydroxyphenyl)ethynyl]-4-(2-phenyl ethynyl)benzene (mw=194.24g/mol, v=0.2 mol, m=58.8 gr) and triethylamine (Et₃N) (mw=101.24 g/mol,v=0.25 mol, m=48.56 gr) are sequentially added thereto, while thesolution is stirred. Then, the mixture is refluxed for 30 min, anddichloromethane is removed therefrom under reduced pressure. Theobtained brown solid is crystallized from a dichloromethane-ethanolmixed solvent to obtain an intermediate I-5. The yield of theintermediate I-5 is 93%.

Synthesis of Final Compound (Compound 2)

Intermediate I-5 (mw=488.46 g/mol, v=0.1 mol, m=48.5 gr) is suspended ina boiling mixed solvent of 180 ml of acetic acid and 3 L of methanol ina 5 L flask. Subsequently, a small amount of iron powder (mw=55.85g/mol, v=0.8 mol, m=44.68 gr) is added to the suspension, and 100 ml ofwater is added thereto. Then, the mixture is refluxed for 5 h, and 500ml of the water is further added thereto. When the reaction is complete,1 L of water is further added thereto, the mixture is cooled to obtain asolid, and the solid is collect by filtration. Subsequently, theobtained solid is suspended in 400 ml of boiling iso-propanol and thenfiltered while being cooled, which is repeated three times. The obtainedproduct is dissolved in 300 ml of dimethyl acetamide and filtered, andthen reprecipitated in 2 L of water. The obtained precipitate iscollected by filtration and then suspended in iso-propanol to removewater. Subsequently, the obtained product is collected by filtration,and the obtained solid is suspended in 600 ml of boiling methanol andthen filtered while being cooled. The obtained product is dried at 70°C. under vacuum to obtain compound 2. The yield of compound 2 is 65.4%.

¹H NMR (DMSO-de) 300 MHz, δ, ppm: 4.92 (br. s, 4H, NH₂), 5.88 (dd, 1H,J¹³=1.8 Hz), 6.00 (d, 2H, J¹³=1.8 Hz), 7.42-7.60 (m, 13H).

Synthesis Example 3: Synthesis of Compound 3 Synthesis of IntermediateI-6

3.5-dinitrobenzoic acid (mw=212.12 g/mol, v=0.2 mol, m=42.42 gr),phosphorus pentachloride (PCl₅, mw=208.24 g/mol, v=0.2 mol, m=41.65 gr),and one drop of pyridine are added to 300 ml of toluene, and the mixtureis stirred and refluxed for 12 h. Subsequently, the toluene and POCl₃are removed under reduced pressure, and the remaining residue isdissolved in 1 L of dichloromethane. Subsequently,4-hydroxydiphenylacetylene (mw=194.24 g/mol, v=0.2 mol, m=38.85 gr), andtriethylamine (Et₃N) (mw=101.24 g/mol, v=0.25 mol, m=48.56 gr) aresequentially added thereto while the solution is stirred. Then, themixture is refluxed for 30 min, and dichloromethane is removed therefromunder reduced pressure. The obtained brown solid is crystallized from adichloromethane-ethanol mixed solvent to obtain an intermediate I-6. Theyield of the intermediate I-6 is 95%.

Synthesis of Final Compound (Compound 3)

Intermediate I-6 (mw=388.34 g/mol, v=0.1 mol, m=38.8 gr) is suspended ina boiling mixed solvent of 180 ml of acetic acid and 2 L of methanol ina 5 L flask. Subsequently, a small amount of iron powder (mw=55.85g/mol, v=0.8 mol, m=44.68 gr) is added to the suspend solution, and 100ml of water is added thereto. Then, the mixture is refluxed for 3 h, and500 ml of water is further added thereto. When the reaction is complete,1 L of water is further added thereto, and the mixture is cooled andthen extracted three times with 600 ml of ethyl acetate. The extractedsolution is washed with water, dried with Na₂SO₄ and then concentratedunder reduced pressure to obtain a white solid. The white solidprecipitate is collected by filtration and washed with a small amount ofcold ethyl acetate to obtain compound 3. The yield of the compound 3 is60%.

¹H NMR (DMSO-d₆) 300 MHz, δ, ppm: 4.92 (br. s, 4H, NH₂), 5.88 (dd, 1H,J¹³=1.8 Hz), 6.00 (d, 2H, J¹³=1.8 Hz), 7.44-7.59 (m, 13H).

Synthesis Example 4: Synthesis of Compound 4 Synthesis of IntermediateI-7

Phenylacetylene (mw=102.14 g/mol, v=0.197 mol, m=20.1 gr) and3,5-dinitrobromobenzene (mw=247.01 g/mol, v=0.164 mol, m=40.5 gr) aredissolved in a mixed solvent of 300 ml of triethylamine and 100 ml ofTHF in a 1 L round-bottomed flask to prepare a solution. The solution ispurged with dry nitrogen gas for 1 h. Subsequently, palladium(II)chloride (PdCl₂, mw=177.33 g/mol, v=0.00164 mol, m=0.29 gr), copper(I)iodide (Cul) (mw=190.45 g/mol, v=0.00328 mol, m=0.62 gr), andtriphenylphosphine (PPh₃, mw=262.45 g/mol, v=0.00656 mol, m=1.72 gr) aresequentially added to the solution, and the mixture is refluxed at 100°C. for 24 h under a nitrogen atmosphere. When the reaction is complete,triethylamine is removed under reduced pressure, and the remaining solidis washed. The obtained product is suspended in boiling ethyl acetateand then filtered while being cooled, which is repeated twice. Then, theproduct obtained therefrom is dried at 80° C. under vacuum to obtain ayellow crystalline solid of an intermediate I-7. The yield of theintermediate I-7 is 75%.

Synthesis of Final Compound (Compound 4)

Intermediate I-7 (mw=268.25 g/mol, v=0.112 mol, m=30 gr) is suspended ina boiling mixed solvent of 180 ml of acetic acid and 2 L of methanol ina 5 L flask. Subsequently, iron powder (mw=55.85 g/mol, v=0.896 mol,m=50 gr) is added to the suspension, and 100 ml of water is addedthereto. The mixture is refluxed for 3 h, and 500 ml of water is furtheradded thereto. When the reaction is complete, 1 L of water is addedthereto, and the mixture is cooled and then extracted three times with600 ml of ethyl acetate. The extracted solution is washed with water,and solvent is removed therefrom under reduced pressure. Then, 2equivalents of concentrated hydrochloric acid are added to the productobtained therefrom to obtain a precipitate. The precipitate is suspendedin boiling acetone and then collected by filtration. The obtained solidis dissolved in 1 L of hot water and treated with charcoal, and thenfiltered. Subsequently, an ammonium hydroxide aqueous solution is addedthereto to obtain a white precipitate. The precipitate is filtered andwashed with water and then dried at 70° C. for 24 h under a reducedpressure to obtain compound 4.

¹H NMR (DMSO-d6) 300 MHz, δ, ppm: 4.90 (br. s, 4H, NH₂), 5.87 (dd, 1H,J¹³=1.8 Hz), 5.99 (d, 2H, J¹³=1.8 Hz), 7.37-7.50 (m, 5H).

Synthesis of Polymer Synthesis Example 5

Compound 1 according to Synthesis Example 1 and the compound 5represented by Chemical Formula A-1(2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl, Tokyo ChemicalIndustry) in a mole ratio of 5:5 are dissolved in dimethyl acetamide toprepare a solution. The compound 6 represented by Chemical Formula B-1(4,4′-oxydiphthalic anhydride, Tokyo Chemical Industry) is addedthereto, and the mixture is reacted at room temperature for 48 h toprepare a composition. The composition includes compound 1, compound 5,and compound 6 in a mole ratio of 5:5:10. When the reaction is complete,the composition is spin coated on a 5×5 square centimeters (cm²) glassplate at 1,000 revolutions per minute (rpm) for 1 minute (min) and driedin an 80° C. oven for 2 h to form a 15 micrometer (μm)-thick polymerfilm.

The polymer has a structural unit of Chemical Formula C-1 and a weightaverage molecular weight of 260,000 g/mol.

Synthesis Example 6

A polymer film is formed according to the same method as SynthesisExample 5, except for including compound 1, compound 5, and compound 6in a mole ratio of 1:9:10. The polymer has a structural unit of ChemicalFormula C-2 and a weight average molecular weight of 280,000 g/mol.

Synthesis Example 7

A polymer film is prepared according to the same method as SynthesisExample 5, except for including compound 1, compound 5, and compound 6in a mole ratio of 2:8:10. The polymer has a structural unit of ChemicalFormula C-3 and a weight average molecular weight of 270,000 g/mol.

Synthesis Example 8

A polymer film is prepared according to the same method as SynthesisExample 5, except for including compound 1, compound 5, and compound 6in a mole ratio of 3:7:10. The polymer has a structural unit of ChemicalFormula C-4 and a weight average molecular weight of 250,000 g/mol.

Synthesis Example 9

A polymer film is prepared according to the same method as SynthesisExample 5, except for including compound 1, compound 5, and compound 6in a mole ratio of 4:7:10. The polymer has a structural unit of ChemicalFormula C-5 and a weight average molecular weight of 270,000 g/mol.

Synthesis Example 10

Compound 3 according to Synthesis Example 3 and compound 7 representedby Chemical Formula A-2 (4,4′-oxydianiline, Sigma-Aldrich Co. Ltd.) in amole ratio of 1:9 are dissolved in dimethyl acetamide to prepare asolution. Compound 8 represented by Chemical Formula B-2(benzene-1,2,4,5-tetracarboxylic dianhydride, Sigma-Aldrich Co., Ltd.)is added thereto, and the mixture is reacted at room temperature for 48h under a nitrogen atmosphere to prepare a composition. The compositionincludes compound 3, compound 7, and compound 8 in a mole ratio of1:9:10. When the reaction is complete, the composition is spin coated ona 5×5 cm² glass plate at 1,000 rpm for 1 min and dried in an 80° C. ovenfor 2 h to form a 15 μm-thick polymer film.

The polymer has a structural unit of Chemical Formula D-1 and a weightaverage molecular weight of 240,000 g/mol.

Synthesis Example 11

A polymer film is prepared according to the same method as SynthesisExample 10, except for including compound 3, compound 7, and compound 8in a mole ratio of 2:8:10. The polymer has a structural unit of ChemicalFormula D-2 and a weight average molecular weight of 260,000 g/mol.

Compensation Film Example 1

The polymer film according to Synthesis Example 5 is detached from theglass plate and cut to a size of 15×45 square millimeters (mm²) toobtain a sample, and an elongated compensation film having an averagethickness of about 12 μm is prepared by fixing the long side of thesample at a metal frame, putting it in an oven under a nitrogenatmosphere, and heating it up to 300° C. at 10 degree Centigrade perminute (° C./min) for 1 h.

Example 2

An elongated compensation film is prepared according to the same methodas Example 1, except for using the polymer film according to SynthesisExample 6 instead of the polymer film according to Synthesis Example 5.

Example 3

An elongated compensation film is prepared according to the same methodas Example 1, except for using the polymer film according to SynthesisExample 7 instead of the polymer film according to Synthesis Example 5.

Example 4

An elongated compensation film is prepared according to the same methodas Example 1, except for using the polymer film according to SynthesisExample 8 instead of the polymer film according to Synthesis Example 5.

Example 5

An elongated compensation film is prepared according to the same methodas Example 1, except for using the polymer film according to SynthesisExample 9 instead of the polymer film according to Synthesis Example 5.

Example 6

An elongated compensation film is prepared according to the same methodas Example 1, except for using the polymer film according to SynthesisExample 10 instead of the polymer film according to Synthesis Example 5.

Example 7

An elongated compensation film is prepared according to the same methodas Example 1, except for using the polymer film according to SynthesisExample 11 instead of the polymer film according to Synthesis Example 5.

Evaluation Evaluation 1

The retardation values of the compensation films according to Examples 1to 7 are measured.

The retardation value is measured by using Axoscan equipment (AxometricsInc.). The reference wavelength of the retardation is about 550nanometers (nm).

The results are provided in Table 1.

TABLE 1 In-plane retardation Thickness direction retardation (R_(o), nm)(R_(th), nm) Example 1 138 65 Example 2 137 65 Example 3 138 66 Example4 142 68 Example 5 139 67 Example 6 137 64 Example 7 135 63

Referring to Table 1, the compensation films according to Examples 1 to7 have in-plane retardation values ranging from about 110 to 160 nm andmay be used as a λ/4 phase delay layer.

Evaluation 2

The wavelength dispersion values of the compensation films according toExamples 1 to 7 are evaluated.

The wavelength dispersion value is measured by using Axoscan equipment(Axometrics Inc.).

The results are provided in Table 2.

TABLE 2 R (450 nm)/R (550 nm) R (650 nm)/R (550 nm) Example 1 0.84 1.06Example 2 1.07 0.96 Example 3 1.04 0.96 Example 4 1.01 0.95 Example 51.00 0.98 Example 6 1.05 0.98 Example 7 0.95 0.98

Referring to Table 2, the compensation films according to Examples 1 to7 show different retardation values depending on a wavelength, andspecifically, the compensation films according to Examples 1 and 7 havea reverse wavelength dispersion phase delay of which retardationregarding light at a long wavelength is larger than retardationregarding light at a short wavelength, and the compensation filmsaccording to Examples 2 to 6 show a normal wavelength dispersion phasedelay of which retardation regarding light at a long wavelength issmaller than retardation regarding light at a short wavelength.

While this disclosure has been described in connection with what ispresently considered to be practical exemplary embodiments, it is to beunderstood that the invention is not limited to the disclosedembodiments, but, on the contrary, is intended to cover variousmodifications and equivalent arrangements included within the spirit andscope of the appended claims.

What is claimed is:
 1. A monomer represented by Chemical Formula 1-1:

wherein, in Chemical Formula 1-1, Z is —C═O—, —(C═O)O—, —O(C═O)—,—CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—, —CH═CH—, —CF═CF—, or —C(═O)NR^(a)—, L¹and L² are independently a single bond, a substituted or unsubstitutedC1 to C20 alkylene group, a substituted or unsubstituted C1 to C20oxyalkylene group, a substituted or unsubstituted C3 to C20cycloalkylene group, a substituted or unsubstituted C3 to C20oxycycloalkylene group, a substituted or unsubstituted C6 to C20 arylenegroup, a substituted or unsubstituted C6 to C20 oxyarylene group, asubstituted or unsubstituted C3 to C20 divalent heterocyclic group, or acombination thereof, R¹ to R⁶ and R^(a) are independently hydrogen, asubstituted or unsubstituted C1 to C20 alkyl group, a substituted orunsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C2to C20 alkoxyalkyl group, a substituted or unsubstituted C1 to C20fluoroalkyl group, a substituted or unsubstituted C3 to C20 cycloalkylgroup, a substituted or unsubstituted C3 to C20 cycloalkyloxy group, asubstituted or unsubstituted C4 to C20 cycloalkoxyalkyl group, asubstituted or unsubstituted C6 to C20 aryl group, a substituted orunsubstituted C6 to C20 aryloxy group, a substituted or unsubstituted C7to C20 arylalkyl group, a substituted or unsubstituted C7 to C20aryloxyalkyl group, a substituted or unsubstituted C3 to C20heterocyclic group, a substituted or unsubstituted silyl group, ahydroxy group, a halogen, a nitro group, or a combination thereof, n andm are independently 0 or 1, p is an integer ranging from 1 to 3, a to fare independently integers ranging from 0 to 4, and a+b, c+d, and e+fare independently integers of less than or equal to
 4. 2. The monomer ofclaim 1, wherein the monomer is represented by Chemical Formula 1-1a or1-1b:

wherein, in Chemical Formulae 1-1a and 1-1b, Z is —C═O—, —(C═O)O—,—O(C═O)—, —CH₂O—, —CF₂O—, —OC(═O)O—, —C≡C—, —CH═CH—, —CF═CF—, or—C(═O)NR^(a)—, L¹ and L² are independently a single bond, a substitutedor unsubstituted C1 to C20 alkylene group, a substituted orunsubstituted C1 to C20 oxyalkylene group, a substituted orunsubstituted C3 to C20 cycloalkylene group, a substituted orunsubstituted C3 to C20 oxycycloalkylene group, a substituted orunsubstituted C6 to C20 arylene group, a substituted or unsubstituted C6to C20 oxyarylene group, a substituted or unsubstituted C3 to C20divalent heterocyclic group, or a combination thereof, R¹ to R⁶ andR^(a) are independently hydrogen, a substituted or unsubstituted C1 toC20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group,a substituted or unsubstituted C2 to C20 alkoxyalkyl group, asubstituted or unsubstituted C1 to C20 fluoroalkyl group, a substitutedor unsubstituted C3 to C20 cycloalkyl group, a substituted orunsubstituted C3 to C20 cycloalkyloxy group, a substituted orunsubstituted C4 to C20 cycloalkoxyalkyl group, a substituted orunsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6 toC20 aryloxy group, a substituted or unsubstituted C7 to C20 arylalkylgroup, a substituted or unsubstituted C7 to C20 aryloxyalkyl group, asubstituted or unsubstituted C3 to C20 heterocyclic group, a substitutedor unsubstituted silyl group, a hydroxy group, a halogen, a nitro group,or a combination thereof, p is an integer ranging from 1 to 3, a to fare independently integers ranging from 0 to 4, and a+b, c+d, and e+fare independently integers of less than or equal to
 4. 3. The monomer ofclaim 1, wherein the monomer is represented by Chemical Formula 1a or1b: